{"id":32879,"date":"2022-12-19T14:02:50","date_gmt":"2022-12-19T14:02:50","guid":{"rendered":"https:\/\/easydmarc.com\/blog\/?p=32879"},"modified":"2025-03-07T09:02:54","modified_gmt":"2025-03-07T09:02:54","slug":"how-to-do-penetration-testing-step-by-step","status":"publish","type":"post","link":"https:\/\/easydmarc.com\/blog\/how-to-do-penetration-testing-step-by-step\/","title":{"rendered":"How to Do Penetration Testing Step by Step"},"content":{"rendered":"<p><span style=\"font-weight: 400;\">Technology evolves for both the good and bad. Tech gurus create new software and systems to make processes more accessible, efficient, and precise; while on the other hand, hackers evolve their techniques to exploit IT infrastructure weaknesses.\u00a0<\/span><\/p>\n<p><span style=\"font-weight: 400;\">That\u2019s why companies invest in <\/span><b>penetration testing activities<\/b><span style=\"font-weight: 400;\">\u2014to spot and fix vulnerabilities before threat actors exploit them.<\/span><\/p>\n<p><span style=\"font-weight: 400;\">This blog will help you learn <\/span><b>how to do penetration testing step by step<\/b><span style=\"font-weight: 400;\">, but first, let\u2019s see <\/span><a href=\"https:\/\/easydmarc.com\/blog\/what-is-penetration-testing-and-why-is-it-important\/\" target=\"_blank\" rel=\"noopener\"><span style=\"font-weight: 400;\">what penetration testing is<\/span><\/a><span style=\"font-weight: 400;\">.<\/span><\/p>\n<h2><b>What is Penetration Testing?<\/b><\/h2>\n<p><span style=\"font-weight: 400;\">Penetration testing, or pentesting for short, is a simulated cyberattack technique where an expert identifies vulnerabilities in an IT structure to fix them before someone uses them to their advantage.\u00a0<\/span><\/p>\n<p><span style=\"font-weight: 400;\">They mimic an attack by following all the possible paths through which hackers can infiltrate a system. Pentesting also assesses the ability of bad actors to breach a system unseen as many cyberattacks occur without an organization\u2019s knowledge.\u00a0<\/span><\/p>\n<p><span style=\"font-weight: 400;\">Like anything, there are several <\/span><a href=\"https:\/\/easydmarc.com\/blog\/benefits-and-risks-of-penetration-testing\/\" target=\"_blank\" rel=\"noopener\"><span style=\"font-weight: 400;\">risks and benefits of penetration testing<\/span><\/a><span style=\"font-weight: 400;\">. Still, in today\u2019s cyber landscape, the pros typically outweigh the cons.<\/span><\/p>\n<p><span style=\"font-weight: 400;\">You can imagine pentesting as a situation where a millionaire secures all the points a burglar can use to enter their mansion. They\u2019ll check all the windows, doors, basements, AC ducts, chimneys, roofs, etc. to ensure nobody can break into their building.<\/span><\/p>\n<p><span style=\"font-weight: 400;\">Now, let\u2019s go through the steps required to <\/span><b>perform penetration testing<\/b><span style=\"font-weight: 400;\">.<\/span><\/p>\n<h2><b>Step 1: Planning<\/b><\/h2>\n<p><span style=\"font-weight: 400;\">Planning is the first step and a vital process in pentesting.<\/span><\/p>\n<p><span style=\"font-weight: 400;\">To secure your IT infrastructure from potential attacks,\u00a0 you need to plan everything in advance. Here\u2019s what\u2019s outlined before starting the actual test.<\/span><\/p>\n<h3><b>What Are You Testing?<\/b><\/h3>\n<p><span style=\"font-weight: 400;\">The process starts by understanding what information assets are present in an IT structure and how to classify them. Determining factors include the business functions they support, asset owners, and the sensitivity and criticality of each asset to the organization.\u00a0<\/span><\/p>\n<p><span style=\"font-weight: 400;\">An information asset is defined as any asset used to store, handle, or process data typically required to perform critical business functions (CBFs). These include servers, storage media, databases, computers, user devices, email communications, and paperwork records.<\/span><\/p>\n<p><span style=\"font-weight: 400;\">That\u2019s why in-depth quantitative and\/or qualitative analyses of each IT asset is also crucial for accurate classification.<\/span><\/p>\n<p><span style=\"font-weight: 400;\">Ultimately, asset classification helps determine what, when, and how often to <\/span><b>perform penetration testing <\/b><span style=\"font-weight: 400;\">based on the following factors:<\/span><\/p>\n<ul>\n<li style=\"font-weight: 400;\" aria-level=\"1\"><span style=\"font-weight: 400;\">The value of an IT asset to various types of cybercriminals.<\/span><\/li>\n<li style=\"font-weight: 400;\" aria-level=\"1\"><span style=\"font-weight: 400;\">The sensitivity and classification of data stored, processed, and passing through the target system.<\/span><\/li>\n<li style=\"font-weight: 400;\" aria-level=\"1\"><span style=\"font-weight: 400;\">The risk level and difficulty associated with the penetration test.<\/span><\/li>\n<\/ul>\n<p><span style=\"font-weight: 400;\">The first two factors determine the risks associated with the probability of a cyberattack and its repercussions (including costs) on business performance.<\/span><\/p>\n<p><span style=\"font-weight: 400;\">The higher the risk, the more important it is to pen &#8211; test the asset in question. This is similar to the millionaire assessing what a burglar can steal and how that would impact their net worth and reputation.\u00a0<\/span><\/p>\n<p><span style=\"font-weight: 400;\">The third factor helps determine the right time to perform<\/span> <span style=\"font-weight: 400;\">the different <\/span><span style=\"font-weight: 400;\">stages of penetration testing<\/span><span style=\"font-weight: 400;\"> to avoid interrupting business processes. Assess whether you\u2019ve got the right workforce to conduct the test or if a third party is required.\u00a0<\/span><\/p>\n<p><span style=\"font-weight: 400;\">Although hiring a third-party expert increases the overall cost, it\u2019s still recommended for high-value asset pentesting.<\/span><\/p>\n<h3><b>Define the Test Elements and Scope<\/b><\/h3>\n<p><span style=\"font-weight: 400;\">IT systems are interlinked, so they often interact with other external and internal frameworks and applications. Also consider the physical, technical, and administrative controls. They\u2019re vital to understanding <\/span><b>how to do penetration testing<\/b><span style=\"font-weight: 400;\"> for the target system.\u00a0<\/span><\/p>\n<p><span style=\"font-weight: 400;\">Pentesters must define the number of attack paths to the system and identify the test elements. This helps them plan which <\/span><span style=\"font-weight: 400;\">penetration testing tools<\/span><span style=\"font-weight: 400;\"> and skills are required.<\/span><\/p>\n<h3><b>Define the Best Outcome<\/b><\/h3>\n<p><span style=\"font-weight: 400;\">The pentester must understand the organization\u2019s expectations from conducting the test. They can seek this by getting answers to these three questions:<\/span><\/p>\n<ol>\n<li style=\"font-weight: 400;\" aria-level=\"1\"><span style=\"font-weight: 400;\">What are the current operational procedures, and how is the company shielding them?<\/span><\/li>\n<li style=\"font-weight: 400;\" aria-level=\"1\"><span style=\"font-weight: 400;\">What are the differences between the protection of current operational procedures and what the organization expects?<\/span><\/li>\n<li style=\"font-weight: 400;\" aria-level=\"1\"><span style=\"font-weight: 400;\">Which security vulnerabilities need to be tested and patched?<\/span><\/li>\n<\/ol>\n<p><span style=\"font-weight: 400;\">You can understand this as what expectations the millionaire would have from the security team they hired to make their house theft-proof. The team evaluates the current security systems to identify any problems, changes, and improvements to meet the expectations of the millionaire.<\/span><\/p>\n<h3><b>What Are You NOT Testing?<\/b><\/h3>\n<p><span style=\"font-weight: 400;\">Although hackers often disrupt critical business operations, most organizations won\u2019t permit that for <\/span><b>network pen tests<\/b><span style=\"font-weight: 400;\">.. For example, exploiting software meant for sales can shut down the entire system, impacting the business until the vulnerability is patched.<\/span><\/p>\n<p><span style=\"font-weight: 400;\">That\u2019s why the organization must clearly define what is permitted and what isn\u2019t during the test. Other test boundaries include what data can be accessed and whether attempted password cracking is allowed.<\/span><\/p>\n<p><span style=\"font-weight: 400;\">If we relate this with the millionaire example, then this situation is where they\u2019ll create specific boundaries for the security team because it would be potentially risky to allow access to bank accounts, safes, or other expensive possessions.<\/span><\/p>\n<h3><b>Get the Project Approved<\/b><\/h3>\n<p><span style=\"font-weight: 400;\">Lastly, irrespective of the<\/span> <span style=\"font-weight: 400;\">penetration testing type<\/span><span style=\"font-weight: 400;\">, an expert must get approval before starting. They should have clear test boundaries, permissions, test elements to be affected, etc.<\/span><\/p>\n<h2><b>Step 2: Attack Simulation<\/b><\/h2>\n<p><span style=\"font-weight: 400;\">The ultimate <\/span><span style=\"font-weight: 400;\">penetration testing goals<\/span><span style=\"font-weight: 400;\"> are to secure essential data from malicious actors and <\/span><a href=\"https:\/\/easydmarc.com\/blog\/top-10-most-common-types-of-cyber-attacks\/\" target=\"_blank\" rel=\"noopener\"><span style=\"font-weight: 400;\">different types of cyberattacks<\/span><\/a><span style=\"font-weight: 400;\">. An ethical hacker performs the simulation in multiple steps that start by collecting passive data and end by analyzing the gaps.\u00a0<\/span><\/p>\n<p><span style=\"font-weight: 400;\">After the planning phase, here\u2019s <\/span><b>how to do penetration testing step by step<\/b><span style=\"font-weight: 400;\">:<\/span><\/p>\n<h3><b>#1: Get Passive Data<\/b><\/h3>\n<p><span style=\"font-weight: 400;\">The first step involves collecting passive information about the target system and company to understand how it works during day-to-day processes.\u00a0<\/span><\/p>\n<p><span style=\"font-weight: 400;\">This process is coined under various terms like discovery, reconnaissance, scanning, or probing but describes the same thing:. assessing the complete operating environment, potential vulnerabilities, and available attack vectors of the target system. Public information can be a valuable resource for cyberattackers, so pentesters must also use such data to their advantage.<\/span><\/p>\n<h3><b>#2: Start the Active Testing Stage<\/b><\/h3>\n<p><span style=\"font-weight: 400;\">In this stage, an ethical hacker tests the various attack paths within the boundaries set by management. It includes both static and dynamic analysis.\u00a0<\/span><\/p>\n<p><span style=\"font-weight: 400;\">In static analysis, internal components of the target IT structure are tested and the attack paths are modeled before evaluating the vulnerabilities. It includes examining application binaries, source code, and byte code for any exploitable weaknesses.<\/span><\/p>\n<p><span style=\"font-weight: 400;\">Conversely, dynamic analysis involves <\/span><b>penetration testing activities<\/b><span style=\"font-weight: 400;\"> performed while a program is in operation. It includes examining and attacking a system in its running state to find any security vulnerabilities.\u00a0<\/span><\/p>\n<p><span style=\"font-weight: 400;\">Deploying malware via email, brute force attacks, Denial-of-Service (DoS) attacks, control bypass attempts, and any other active penetration tactics may fall under this step.\u00a0<\/span><\/p>\n<p><span style=\"font-weight: 400;\">Once the pentester gains access to the target system, all other identified attack pathways and assets must be scanned, mapped, identified, and tested.\u00a0<\/span><\/p>\n<h3><b>#3: Analyze the Data<\/b><\/h3>\n<p><span style=\"font-weight: 400;\">Next, the testing team evaluates the collected test result data to understand attack paths and how threat actors can compromise system components within the target structure.<\/span><\/p>\n<h3><b>#4: Assess Access Outcomes<\/b><\/h3>\n<p><span style=\"font-weight: 400;\">Here, outcomes of any interactions between the target structure and the other operating system elements identified in the previous steps are analyzed. This step also assesses the types of connections, how they\u2019re secured, and any exchanged data.<\/span><\/p>\n<h3><b>#5: Correlate the Gathered Information<\/b><\/h3>\n<p><span style=\"font-weight: 400;\">Pentesters must then reconcile the collected information. This data, correlated with all the previous steps, help get a clear picture of the system, its operating environment, and its vulnerable aspects.\u00a0<\/span><\/p>\n<h3><b>#6: Create Safe Operation KPIs<\/b><\/h3>\n<p><span style=\"font-weight: 400;\">Next, the ethical hacking team determines how optimum protection can be achieved based on the analyzed data. They create metrics to measure current and future states at which the system can safely operate. This state is either created or reviewed.<\/span><\/p>\n<h3><b>#7: Perform Gap Analysis<\/b><\/h3>\n<p><span style=\"font-weight: 400;\">The last step in attack simulation is gap analysis. Here, pentesters must assess how the system should operate and be protected versus its current state to identify security gaps.<\/span><\/p>\n<h2><b>Step 3: Reporting and Risk Analysis<\/b><\/h2>\n<p><span style=\"font-weight: 400;\">The gap analysis report is created by assessing any successful cloned attacks. The testing typically compiles two separate reports. The first one is for management; it\u2019s not as technically detailed and contains meaningful, business-related information on the potential impacts of the identified vulnerabilities.<\/span><\/p>\n<p><span style=\"font-weight: 400;\">The second penetration testing report is for the IT team. It includes detailed information on pentesting outcomes to help assess risks and identify solutions to patch security weaknesses.\u00a0<\/span><\/p>\n<p><span style=\"font-weight: 400;\">The report should also contain key metrics to help the organization conduct risk analysis, classify the severity of each identified risk, and identify the best solutions for the most significant risk reduction.<\/span><\/p>\n<h2><b>Step 4: Retesting<\/b><\/h2>\n<p><span style=\"font-weight: 400;\">Once the report is submitted, remediation recommendations are followed by the company\u2019s IT team to patch the identified security weaknesses. Retesting is then conducted after 2-3 months to check whether the vulnerabilities have been effectively remediated.<\/span><\/p>\n<h2><b>Summary<\/b><\/h2>\n<p><b>Performing penetration testing<\/b><span style=\"font-weight: 400;\"> is a vital part of cyber protection. It helps identify vulnerabilities hackers can exploit to breach your systems, gain unauthorized control, access confidential data, and ultimately harm your organization.\u00a0\u00a0<\/span><\/p>\n<p><span style=\"font-weight: 400;\">Pentesting starts with in-depth planning like understanding what has to be tested, the elements and risks involved, and the boundaries set by the management team.<\/span><\/p>\n<p><span style=\"font-weight: 400;\">The actual test begins by collecting and analyzing passive data to actively simulating an attack and then correlating the gathered information. This helps in setting metrics to measure current and future states for optimum protection.\u00a0<\/span><\/p>\n<p><span style=\"font-weight: 400;\">Once the test is conducted, it\u2019s crucial to analyze the security risks and identify optimal solutions. Your IT team should follow the remedial recommendations to ensure your systems are attack-proof. <\/span><\/p>\n","protected":false},"excerpt":{"rendered":"<p>Technology evolves for both the good and bad. &#8230;<\/p>\n","protected":false},"author":6,"featured_media":32880,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"inline_featured_image":false,"footnotes":""},"categories":[204,199,446],"tags":[],"class_list":["post-32879","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-blog","category-cybersecurity","category-penetration-testing"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO Premium plugin v27.4 (Yoast SEO v27.4) - https:\/\/yoast.com\/product\/yoast-seo-premium-wordpress\/ -->\n<title>How to Do Penetration Testing Step by Step | EasyDMARC<\/title>\n<meta name=\"description\" content=\"Understand how to conduct penetration testing with EasyDMARC\u2019s step-by-step guide. 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